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Chesapeake Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Chesapeake holiday rentals

A living room with a patterned rug, a coffee table, and a bookshelf.

1. Espresso Maker & Modern Decor by Arena, University, Hospitals

Espresso Maker & Modern Decor by Arena, University, Hospitals
Huntington
10.0 out of 10, Exceptional, (4 reviews)
"The place was very cozy and had everything you would need for your stay"
United States
Kellie V.
The price is NZ$544
includes taxes & fees
17 Oct - 18 Oct
Espresso Maker & Modern Decor by Arena, University, Hospitals
A fountain with water jets in a park area, surrounded by stone walls and greenery.

2. The Blue House/Eclectic Art /Huntington’s Best Parks/full refund 1 day out

The Blue House/Eclectic Art /Huntington’s Best Parks/full refund 1 day out
Huntington
10.0 out of 10, Exceptional, (23 reviews)
"Lovely and quiet location, comfortable, most stocked VRBO we’ve ever stayed in!"
United States
Lesly-Marie
The price is NZ$450
includes taxes & fees
2 Nov - 3 Nov
The Blue House/Eclectic Art /Huntington’s Best Parks/full refund 1 day out
A modern kitchen with white cabinets, stainless steel appliances, and a central island.

3. Quaint, spacious, & relaxing; come stay with us, you'll enjoy the details.

Quaint, spacious, & relaxing; come stay with us, you'll enjoy the details.
South Point
10.0 out of 10, Exceptional, (20 reviews)
"The apartment was nice and clean. Bed was comfortable. Very peaceful neighbor hood. Lovely place to stay better than any hotel. Would stay there again for sure."
United States
teresa lynette
The price is NZ$231
includes taxes & fees
17 Oct - 18 Oct
Quaint, spacious, & relaxing; come stay with us, you'll enjoy the details.
A covered outdoor seating area with wicker furniture and a decorative wall with hanging plants.

4. Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes

Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes
Huntington
9.6 out of 10, Exceptional, (8 reviews)
"Great space for family gathering for our Marshall grad. Very cute, spacious and centrally located."
United States
Carrie S.
The price is NZ$568
includes taxes & fees
3 Nov - 4 Nov
Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes
A living room with a sofa, coffee table, and a chandelier. There is a painting on the wall and a window with curtains.

5. Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital

Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital
Huntington
8.8 out of 10, Excellent, (3 reviews)
"Property was exactly as described. Wish we would have found it sooner. Will definitely be back. Nice cozy place and very affordable. "
United States
richie k.
The price is NZ$598
includes taxes & fees
18 Oct - 19 Oct
Aparthotel: Lopsy Blue -by Arena/Marshall/Hospital
A living room with a sofa, coffee table, and a chandelier.

6. Historic & Chic apartment by Arena, University, Hospital - Dog Friendly

Historic & Chic apartment by Arena, University, Hospital - Dog Friendly
Huntington
9.6 out of 10, Exceptional, (8 reviews)
"Very nicely decorated, cozy and clean."
United States
Yvette H.
The price is NZ$552
includes taxes & fees
2 Nov - 3 Nov
Historic & Chic apartment by Arena, University, Hospital - Dog Friendly
A modern kitchen with a central island, built-in appliances, and pendant lighting.

7. Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland

Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland
Ashland
10.0 out of 10, Exceptional, (23 reviews)
"Great place to stay. Very modern and comfortable. Philip is a nice guy to deal with."
United States
Paul M.
The price is NZ$330
includes taxes & fees
17 Oct - 18 Oct
Renovated Apartment with Modern Amenities, Fenced-In Back Yard -Downtown Ashland
A kitchen with a granite countertop, a black faucet, and a window with a view of a forest.

8. 2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.

2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.
Kenova
10.0 out of 10, Exceptional, (63 reviews)
"Very nice place to stay! We really enjoyed it! "
United States
Hannah M.
The price is NZ$365
includes taxes & fees
2 Nov - 3 Nov
2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.
A cozy cabin-style room with a bed, a small table, a chair, and a trash bin.

9. Hot Tub, Fire Pit: Lake-View Catlettsburg Getaway!

Hot Tub, Fire Pit: Lake-View Catlettsburg Getaway!
Catlettsburg
10.0 out of 10, Exceptional, (9 reviews)
"Great little place to spend a few days very clean...im a very picking person and it was a 10 in every way...."
United States
Lance G.
The price is NZ$454
includes taxes & fees
19 Oct - 20 Oct
Hot Tub, Fire Pit: Lake-View Catlettsburg Getaway!
A white cabinet with two drawers and a coffee maker on top.

10. The Park House A 5 Bedroom Retreat w/Game Room

The Park House A 5 Bedroom Retreat w/Game Room
Huntington
10.0 out of 10, Exceptional, (24 reviews)
"Beautiful place, loved the decor and home away from home."
United States
Yvette H.
The price is NZ$1,290
includes taxes & fees
22 Oct - 23 Oct
The Park House A 5 Bedroom Retreat w/Game Room
A hot tub with a control panel and a wooden cabinet.

11. Charming Home with private Hot Tub and Fire Pit

Charming Home with private Hot Tub and Fire Pit
South Point
10.0 out of 10, Exceptional, (17 reviews)
"The cleanliness and the small special items example the bottle of wine and snacks if we wanted them. Will definitely stay here again if we travel that way. "
United States
Elizabeth C.
The price is NZ$320
includes taxes & fees
25 Oct - 26 Oct
Charming Home with private Hot Tub and Fire Pit
A wooden deck with a table and chairs, overlooking a calm lake with trees and buildings in the background.

12. Large Cabin with Stunning View - Fire Pit, Relax & Unwind

Large Cabin with Stunning View - Fire Pit, Relax & Unwind
Gallipolis
9.8 out of 10, Exceptional, (56 reviews)
"It’s a wonderful place to stay so peaceful and relaxing hate to leave"
United States
Tess
The price is NZ$296
includes taxes & fees
22 Oct - 23 Oct
Large Cabin with Stunning View - Fire Pit, Relax & Unwind
A wooden deck with a glass table and chairs, a thatched umbrella, and a grill.

13. Charming 2-bedroom house located in beautiful wooded setting!

Charming 2-bedroom house located in beautiful wooded setting!
Raceland
10.0 out of 10, Exceptional, (22 reviews)
"We really enjoyed our stay, perfect location for a visit to that part of Kentucky."
United States
Melinda K.
The price is NZ$353
includes taxes & fees
20 Oct - 21 Oct
Charming 2-bedroom house located in beautiful wooded setting!
A dining area with a round table, a vase with flowers, a lamp, and a potted plant.

14. Charming 3BR Home - Near KDMC & Downtown

Charming 3BR Home - Near KDMC & Downtown
Ashland
8.8 out of 10, Excellent, (8 reviews)
"It was in a quiet neighborhood. The beds were comfortable."
United States
Judi
The price is NZ$332
includes taxes & fees
20 Oct - 21 Oct
Charming 3BR Home - Near KDMC & Downtown
A dining table with a woven basket containing a candle and a book. A fireplace with a tiled surround is visible in the background.

15. Huntington Modern History - 4BD, MU, DT, St Mary's

Huntington Modern History - 4BD, MU, DT, St Mary's
Huntington
10.0 out of 10, Exceptional, (14 reviews)
"It was a great, historic home. We loved how the owners have kept the original details and the space worked very well for a family of four. "
United States
Brian B.
The price is NZ$1,220
includes taxes & fees
18 Oct - 19 Oct
Huntington Modern History - 4BD, MU, DT, St Mary's
A wooden fence with decorative picket tops and string lights.

16. Cozy With A Little Touch of Love

Cozy With A Little Touch of Love
Huntington
7.8 out of 10, Good, (6 reviews)
"Had a nice weekend stay here while in Huntington working. It was nice an quiet! Landlord was great!"
United States
Amanda P.
The price is NZ$776
includes taxes & fees
18 Oct - 19 Oct
Cozy With A Little Touch of Love
A rustic cabin with a fire pit and outdoor seating.

17. Secluded Ohio Forest Escape at Fuller's Fifty

Secluded Ohio Forest Escape at Fuller's Fifty
Patriot
10.0 out of 10, Exceptional, (100 reviews)
"Very beautiful place everything that you need to have a small getaway or a long getaway. "
United States
Anthony R.
The price is NZ$337
includes taxes & fees
19 Oct - 20 Oct
Secluded Ohio Forest Escape at Fuller's Fifty
A bedroom with a bed, bedside table, nightstand, lamp, and a ceiling fan.

18. The Cedar House -Cute, inviting, Charming and memorable.

The Cedar House -Cute, inviting, Charming and memorable.
Barboursville
The price is NZ$530
includes taxes & fees
23 Oct - 24 Oct
The Cedar House -Cute, inviting, Charming and memorable.
A living room with a sofa, coffee table, and a chandelier.

19. Entire Bldg w/6 Bedrooms across 4 Separate Apts - Group/Corporate Stay Downtown

Entire Bldg w/6 Bedrooms across 4 Separate Apts - Group/Corporate Stay Downtown
Huntington
The price is NZ$2,581
includes taxes & fees
18 Oct - 19 Oct
Entire Bldg w/6 Bedrooms across 4 Separate Apts - Group/Corporate Stay Downtown
A covered porch with a wooden railing, a table with four chairs, and a hanging planter.

20. Cozy Fonzie Flat

Cozy Fonzie Flat
Ashland
10.0 out of 10, Exceptional, (1 review)
"It was a very pleasant stay, it was well maintained and clean. The property manager answered my questions quickly and efficiently,also was very professional. As a Veteran it was nice to have a place that accepts pets. "
United States
James F.
The price is NZ$567
includes taxes & fees
17 Oct - 18 Oct
Cozy Fonzie Flat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesapeake Hotel Reviews

DoubleTree by Hilton Huntington

DoubleTree by Hilton Huntington

10/10 Excellent
"I thought I was going to write a bad review until I got my bill. This was the most polite and helpful staff I’ve ever dealt with in a hotel, and they made everything right in the end. So, in the end I had a nice clean room, a nice shower (dirty, sweaty work had me showering twice a day), and paid a fair price for it. What I didn’t like was that everything seemed like it was going to be an up charge: I registered online and it showed me breakfast was an option —for $8 per day, but would not let me select it. I informed them and asked for this on check-in, was told I was good to go, and then was given a bill for 2 days of $18 each at each breakfast. I refused to sign but expected I was charged anyway. I was initially upset I spent $8 on breakfast… but I would not pay $18–the breakfast was not very good. Rubbery biscuits, flavorless gravy, hard pancakes, didn’t know I had to ask for coffee so no coffee first breakfast There was no mention that there is no parking lot. Parking… you guessed it, extra $10 a day for a parking garage on the next block that connects via 2nd floor skybridge, and my room was in the 11th floor. So… I had long rough days with a 1,000 yard walk at work for parking, to then have to walk a block when I got back. Good exercise at least. The garage sign that showed hotel parking was illegible at night, and coming back from work at 11pm, I drove around the block for almost an hour before getting good directions from staff, and went to 2 wrong garages first…"
John 4-night trip
Posted less than an hour ago
DoubleTree by Hilton Huntington

Find out more about Chesapeake

Everything you need to know about Chesapeake holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesapeake holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesapeake. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesapeake holiday rentals we have selected for you start as low as NZ$231 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesapeake rentals

At Expedia, we put the best Chesapeake holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesapeake rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Chesapeake?

Yes, there are holiday rentals close to the most popular sights in Chesapeake, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chesapeake has to offer?

2BR-1B. Fire Pit With Stunning River View. Minutes From Downtown Huntington.: This holiday home rental outside of Chesapeake is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

What can I see and do in Chesapeake?

Explore the area and family-friendly sights such as Camden Park Amusement Park, or get out into nature at a spot like Ohio River Valley. In the wider area, you’ll find Mountain Health Arena and Pullman Square.

What are holiday rentals like in Chesapeake?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesapeake. Holiday rentals offer amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family getaway.